Monk's obsessed fan Marci Maven (Sarah Silverman) finds herself in trouble when her pet dog is accused of mauling and killing a neighbor, even though the dog died three days before the alleged attack. In desperation, she turns to Monk for answers.

Monk must confront his prejudice against nudists (including Diedrich Bader) when he is called to investigate the murder of a woman on a nude beach. Along the way, he must investigate a computer magnate the victim was trying to talk to (Alfred Molina) and her roommate (Angela Kinsey).

Monk and Natalie find themselves in dangerous waters when they believe that Captain Stottlemeyer's girlfriend Linda Fusco (Sharon Lawrence) murdered her business partner when he decided to leave her and start his own company. There is just one problem: 20 minutes before the murder, Linda was engaged with Monk, Natalie and Stottlemeyer in a webchat from her house, which is way too far away from the crime scene for her to have an adequate time window. Monk must hence try to solve the murder without jeopardizing his friendship with Stottlemeyer.

Monk plays Cupid and detective at the same time, helping Julie out with dating issues surrounding herself and her boyfriend (Matt Lanter) while investigating a sports agent (Vincent Ventresca) that he believes shot his wife and then staged to make it look like she was shot by a burglar who himself was also murdered as part of the coverup.

While Monk is investigating an incident in the woods in which someone has torched the car of a driver who has died in an accident, a famous daredevil previously only known as the Frisco Fly falls while scaling a tall building, and is revealed to be none other than Monk's rival patient Harold Krenshaw (Tim Bagley), turning Monk's world upside-down. It's up to Monk to find out the connection between the two incidents before someone is killed.

When an ex-convict (Tim DeZarn) Monk sent to prison years earlier for a double torture-murder home invasion is cleared by new DNA evidence, Monk helps him rebuild his life, while trying to correct his previous mistake.

It is Natalie's turn to be concerned when two women sharing the same name as her daughter are killed on the same day through completely different M.Os, while her Julie is preparing for her driver's test.

While investigating two murders at a roadside junk shop, Monk takes up a new hobby–painting–and meets with unexpected success with a mysterious Russian art collector.Note: Last appearance of Stanley Kamel as Dr. Charles Kroger

While everyone mourns Monk's "death", Monk goes into hiding to find the proof that will clear his name. He is later led to a vast conspiracy involving the sheriff (Scott Glenn) who framed him, the lieutenant governor, and even Dale "The Whale" Biederbeck (Ray Porter).